Patent GB-605573-A (GB)
Title: Plasticized organic compositions
IPC: C08L101/00
Filed: 1945-07-30
Abstract: Compositions of plastic materials comprise as plasticisers polymeric esters of monobasic organic acids with allyl-type alcohols.  Examples of allyl-type alcohols are allyl alcohol, buten-1-ol-3, 3-methyl-pentene-1-ol-3, 4,41-dimethyl-hexen - 1 - ol - 3, 3 - tolyl - propen - 1 - ol - 3, crotyl, tiglyl and cinnamyl alcohols and butadiene-2,3-ol-1.  Many other examples are given.  Suitable monobasic organic acids are monocarboxylic aliphatic acids, e.g. formic, acetic, chloro- and phenyl-acetic, propionic, chloropropionic, lactic, butyric, isobutyric, valeric, glycolic, acetylglycolic, methoxyacetic, stearic, levulinic, acrylic, propiolic, cinnamic, oleic, linoleic and linolenic acids; cyclo-aliphatic and aromatic acids, e.g. furoic, abietic, benzoic, naphthenic, toluic and salicylic acids; and thiolic acids represented by the formul  R-CO.SH and R-C : S.SH.  The polymeric esters may be prepared by polymerization of the monomers in the presence of peroxide or other usual catalysts, or by esterification of a polymeric allyl-type alcohol, or by ester exchange or interchange. Polymeric esters of the thio acids may be produced from the monomer, but usually by reacting the polymeric allyl-type mercaptan with the desired acid or anhydride. The polymeric mercaptan may be produced by reacting sodium hydrogen sulphide with the polymeric allyl-type chloride or by reacting sulphuric acid with the polymeric allyl-type alcohol, forming the sodium salt and then reacting with sodium hydrogen sulphide.  Mixed esters and esters containing acetal groups, alcoholic hydroxyl groups and halogens may be used.  The polymeric esters may be decolourised and stabilised by catalytic or electrolytic hydrogenation, or may be treated with sulphur, sulphur-containing compounds, halogens or halogen-containing compounds.  Plastic materials which may be plasticised by these polymeric esters include: colophony, shellac, copal, dammar, camphor, rosin, polymerized and hydrogenated rosin, asphalt; regenerated cellulose, cellulose esters and ethers; protein plastics; phenol-aldehyde and urea-formaldehyde resins, alkyd resins, synthetic linear polyamides and polyesters; polymers of ethylene, styrene, a -methylstyrene, dichlorostyrene, vinyl naphthalene, vinyl and vinylidene halides, vinyl and allyl esters of saturated monocarboxylic acids, vinyl ethers, methyl acrylate and methacrylate and allyl halides; polymers of unsaturated polyesters such as the vinyl, allyl and methallyl polyesters of oxalic, malonic, glutaric, adipic, sebasic, citric, tricarballylic, phthalic and naphthalene dicarboxylic acids; polymers of vinyl, allyl and methallyl polyethers of saturated polyhydric alcohols; polymers of unsaturated aliphatic acid polyesters of polyhydric alcohols; polymers of unsaturated aliphatic esters of unsaturated aliphatic acids such as acrylic, crotonic, itaconic, citraconic and cinnamic acids; polymers of vinyl, allyl and methallyl esters of phosphoric acid and of the ortho acids of silicon and boron; silicone resins and polymers of compounds having two or more ethylenic linkages such as vinyl and divinyl acetylene, dienes, chloroprene and isoprene.  Copolymers, modified plastics and mixtures of plastics may be employed in the compositions.  The examples describe compositions including other plasticisers, e.g. tricresyl phosphate and dibutyl phthalate and solvents such as methyl ethyl (or isobutyl) ketone, methyl cellosolve ("Cellosolve" being a Registered Trade Mark); butadiene-acrylonitrile and butadiene-styrene copolymers containing phenyl-beta-naphthylamine, benzthiazyl disulphide or mercaptobenzothiazole, polyallyl acetate, channel black, zinc oxide, stearic acid and sulphur, which are vulcanized; and cellulose acetate compositions comprising as solvents ethyl lactate, methylene chloride, ethanol, acetone, diacetone, methyl acetate, ethylene dichloride, dioxane and nitromethane.  Pigments, fillers and dyes may be included.  The compositions are useful as coating and impregnating compositions, stencil paper, insulating material, phonograph records, films, sheets, filaments and floor coverings.ALSO:Compositions of plastic materials comprise as plasticisers polymeric esters of monobasic organic acids with allyl-type alcohols.  Examples of allyl-type alcohols are allyl alcohol, buten-1-ol-3, 3-methylpenten-1-ol-3, 4. 41-dimethyl-hexen 1-ol-3, 3-tolyl-propen-1-ol-3, crotyl, tiglyl and cinnamyl alcohols and butadiene-21-3-ol-1.  Many other examples are given.  Suitable monobasic organic acids are monocarboxylic aliphatic acids e.g. formic, acetic, chloro-and phenyl-acetic, propionic, chloropropionic, lactic, butyric, isobutyric, valeric, glycolic, acetylglycolic, methoxyacetic, stearic, levulinic, acrylic, propiolic, cinnamic, oleic, linoleic and linolenic acids; cycloaliphatic and aromatic acids, e.g. furoic, abietic, benzoic, naphthenic, toluic and salicylic acids; and thiolic acids represented by the formulae R.CO.SH and R.CS.SH.  Mixed esters and esters containing acetal groups, alcoholic hydroxl groups and halogens may be used.  The polymeric esters may be decolourised and stabilised by catalytic or electrolytic hydrogenation, or may be treated with sulphur, sulphur - containing compounds, halogens or halogen containing compounds. Plastic materials which may be plasticised by these polymeric esters include polymers of compounds having conjugated unsaturated linkages such as the diene hydrocarbons, chloroprene and isoprene and copolymers of these with other compounds (see Group IV(a)).  The examples describe butadieneacrylonitrile and butadiene-styrene copolymer compositions containing polyallyl acetate, phenyl beta-naphthylamine, benzthiazyl disulphide or mercaptobenzothiazole, channel black, zinc oxide, stearic acid and sulphur, which compositions are vulcanised.  Pigments, dyes, stabillisers and other plasticisers may be included in the compositions.